


C is for Crossdressing

by TrashBunny



Series: Hiccup/[character] Kink Alphabet [3]
Category: How to Train Your Dragon (Movies)
Genre: Crossdressing, Crossdressing Kink, Cunnilingus, Domestic Fluff, F/M, Lizard!Stormfly, Lizard!Toothless, Panty Kink, Pegging, Sex Toys, Suit Kink, references to other characters - Freeform
Language: English
Status: Completed
Published: 2014-12-06
Updated: 2014-12-06
Packaged: 2018-02-28 07:50:32
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,153
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2724473
Author URL: https://archiveofourown.org/users/TrashBunny/pseuds/TrashBunny
Summary: <blockquote class="userstuff">
              <p>Tonight is date night for the young couple Hiccup and Astrid, plans for the date are the usual romantic dinner though the couple have twist in mind for their attire.</p>
            </blockquote>





	C is for Crossdressing

**Author's Note:**

> Hiccup works in a facility that focuses on physical therapy and prosthetics while Astrid teaches a self-defense class.

“When are the reservations babe?” Hiccup asked Astrid as he adjusted his mint green lacy panties and started to carefully put his prosthetic through a leg hole of his tights. “Nine.” She said from the bathroom. It was her turn to pick the venue for their date night. The events for the night where a nice dinner at a fancy restaurant that Astrid picked out and a walk around the coast line under the stars. It sounded like a wonderful date night to Hiccup.

Though tonight the couple just had a twist in mind.   
  
“Need help there?” Astrid called as she walked out of the bathroom, wearing blue boxers and a button up white shirt. Her blonde hair was pulled back and her bangs styled to the side in a more masculine fashion than usual. She strode over to her fiance and rather roughly grabbed at his crotch, he hissed, she was able to 'tuck' his appendage away from view and she pulled his tights up to his waist, they helped keep everything in place. It was snug but it worked.

“Thanks babe.” He kissed her. She went into their shared semi-walk-in-closet and dressed herself in black suit pants, and threw on a black waist coat. She retrieved an emerald green tie (one that matched the dress Hiccup has layed out for himself) and wrapped it around her neck. She attempted to tie it but before she could get a real shot at it Hiccup walked up and tied it for her. He grinned.

“Thank you baby.” She kissed his cheek and went to get her socks and black Oxfords on.

Hiccup slid the emerald cocktail dress on, he adjusted his very much padded push-up bra and set it in place. It was mint green and lacy, like the panties. “Help me out here?” Hiccup asked sweetly. Astrid zipped him up. He wriggled in the dress to get it fitting properly. It was a sleek cocktail dress, sleeveless; showing off a galaxy of freckles on Hiccup's shoulders, the neck line did not reach too low, but it was still showing off some of Hiccup's faux cleavage. He accessorized with a silver and emerald necklace, a silver sparkling chain around his wrist and -of course- his diamond engagement ring. It was simple, a men's cut, much the opposite to the rest of his outfit but it fit nicely, and it matched Astrid's feminine cut engagement ring. They joked about who would propose to each other first, though last spring they ended up spontaneously proposing together and picking out matching rings later. He finished his outfit with dark green high-heels.

Hiccup and Astrid where finishing up their make-up. Hiccup had shaved his face smooth, put on concealer, blush, eyeshadow, eyeliner and lipstick. He felt very pretty looking at himself in the mirror, his hair was brushed and styled in a very feminine style, almost pixie cut-ish just longer. He sprayed it slightly just to keep it's shape. He turned to Astrid and smiled, telling her he was ready. She was just finishing up her eyebrows and wore very minimal concealer.

They both said goodbye and 'be back later tonight' to their lizards; Toothless, the black and smooth one, and Stormfly the bright and ridged one. They where both lazing about their large terrarium. On the way out of the apartment Hiccup grabbed a small black purse and a black cover up for the cold, while Astrid grabbed the car keys.

Astrid drove the whole way to a fancy little bistro located downtown but the coast. They answered their reservations and where seated. The table was set with fine plates and silverwear, wine glasses and a candle in the middle. Astrid pulled out Hiccup's chair for him then seated herself. She initiated the waiter and asked for specials. They ordered after taking a while to decide and the waiter poured them some choice wine as they waited for their dinner to be ready.

While they waited the young couple spoke light-heartedly about their day. Hiccup had a busy day, he had taken some measurements and done some test fittings for a little girl's leg braces, she said she had gotten in a skating accident last winter and was still in recovery, she was doing well through her physical therapy. Another fun thing that happened today was that his associate; Dr. Peabody had brought his excitable middle school aged son in for the day, something about his sitter was out and he wouldn't be any trouble. He wasn't really, just asked _a lot_ of questions and ran around the rooms, letting his imagination run wild.

Astrid listened to every word Hiccup said, she giggled when he would start talking with his hands, it was dorky when he did it normally but with his elegantly contoured and made-up face it was kind of gorgeous. When Hiccup was done Astrid told him about her day, about how well all of her students did during class, successfully disarming her, blocking her assaults and even a few of them managed to overcome and defeat a pseudo-attack by her assistant Eret. She said that early that day she had went out with Ruffnut to get lunch at the mall and she hinted that she may have picked something else up that Hiccup would have to wait until they got home to see.

Hiccup was intrigued and -as expected- tried all his Hiccup-y tricks to get her to tell him. She stayed strong and kept her lips tight shut about it. Winking and smirking at him as he stewed in his frustration from not knowing. He guessed everything from a paint-your-own-model dragon toy to a piece of lingerie Astrid would be displaying for him later. Astrid's face did not change no matter what he guessed. He pouted a bit but that soon faded when the food finally arrived. Through the rest of dinner they chatted and exchanged playful glaces between bites. It was kind of like when they first started dating. It was simple and sweet. Hiccup could not help but to gaze at her throughout dinner.

They had finished dinner off with a decadent chocolate confection. Astrid made a point to handle the cheque while she fixed up her tie. Hiccup rolled his eyes at her.

After the dinner the young couple walked, fingers intertwined, along the icey rock inclosed shore. The stars where getting brighter as they left the luminescence of the downtown city behind them. They entered the shore-line park and continued their walk. Hiccup pointed out a few stars for Astrid. They stopped and watched the glittering water for a while. The sky was clear, full of stars, the moon was gloriously bright and the dark water reflected it all. The night was absolutely beautiful. But Hiccup had another thing to look at that was absolutely beautiful.

He pulled Astrid closer and pressed a gentle kiss against her lips (getting some of his lipstick on her), he held it there for a few glorious moments before breaking it and staring deep into her eyes, they where the best blue he had ever seen, and in this moment they where more reflective that the glittering waters beside them. He told her he loved her. Sure he has told her those three words in various ways a countless number of times but every time he meant it. He loved her. He lover her so much and he did not think he could ever put it in words how much he truly did or how often he wanted her to know.

A blush soon crept on his face at the realization of how sappy and emotional he was being. He rubbed the back of his head looked off to the side. Astrid lit up and giggled at him. She grabbed him by the dress front and pulled him close for another kiss. He melted into it. Tasting her still sugary sweet lips with his own, he smelt her cologne and something mixed in that was distinctly Astrid.

They made their way home soon after.

-

As soon as the couple managed into the building they where making out aggressively against the wall. They hap-haphazardly made their way to the bedroom, dropping keys, shoes, a purse, jewelry and coats along the way.

Astrid pushed Hiccup down on the large double bed of their bedroom, falling on top of him. Kissing and rubbing like they where horny teenagers. The times where Hiccup could get hard just from the kissing. But Hiccup had a boner now so nothing has really changed since then except they where now horny adults in drag about to have sex.

They broke the kissing, Astrid got on her feet at the end of the bed and started undoing her belt. Her pants sagged as she pulled it out of the loops, she coiled the leather belt and cracked it against her palm. Just the display and the noise he witnessed made him hard. His erection stiffening upright uncomfortable restricted under the tights. “Wanna get fucked tonight?” She smirked.

“Holy shit babe, y-you. oh my god, yes, oh my god, yes I do please yes.” He stuttered out flustered and god was he really into this right now. Please don't be teasing right now. He pleaded to himself. Sometimes they change things up in their bedroom activities, blindfolds, furry handcuffs maybe some role-play, but Astrid being a dom was Hiccup's favourite naughty thing. Just seeing a women like her in power got him really painfully horny. And she knew it, so she loved to tease him about it.

Astrid made a pleased noise in the back of her throat. She dropped the belt and unbuttoned her pants, she wriggled out of them, she was pretty sexy right now, wearing nothing but boxers and a white button down. She returned to her place on top of him, wrangling him out of the dress. They had to both sit up to get the whole thing off of him. He made quick work of pulling the tights off and went to take his lingerie off but was stopped by Astrid.

“Keep them on.” It wasn’t phased as a questioned and it dripped with command but Hiccup knew she was asking of it was okay. He kept them on and grinned wickedly at her. “Hmm so you wanna keep this going, I'm game.”

He was throbbing in the panties. A clear mark of wetness was starting to form at the tip of the thin fabric and wow he did not realize how turned on he was right now. Damn his fiancee was hot. He wondered if this was getting her wet. Oh no, now he was thinking about her lady-place and how much he wanted to be inside of it. _Woah calm down there Hiccup_. He reeled himself back in, obviously getting ahead of himself with his want. He breathed out shakily.

“Driving you crazy am I?” She flicked his tip and earning a throaty moan. “Wait like a good boy.” She said low.

She positioned herself in his lap, legs spread as she straddled him. “Undo my buttons.” She commanded. “With pleasure,” He was about to say 'm'lady' like he usually does but he stopped himself wondering if that might break up the fantasy. And gods did he not want to break up this fantasy.

He keened suddenly when she started to lightly fondle his crotch. He started undoing her buttons and trying -but mostly failing- to control his hitching as she rubbed on him. God he was dripping pre-cum already. Once all of the buttons where released and her shirt was shrugged off Astrid was nearly bare by now. She stood up, clad in just a white tank top (he could see her pert nipples through the top) and the boxers, no wait, she just turned around and took those off, giving Hiccup a great view of her plush rump. He wanted to squeeze it.

“On the floor.” She ordered. She turned herself around and sat on the bed, crossing a leg over the other, denying Hiccup a view of her treasure. He dropped to his knees in front of her. Looking up at her, daringly raising an eyebrow and giving his usual crooked smile.

“You just going to sit there looking at me or are you going to get to work, hmm?” She hummed at him. Opening her legs. Hiccup did what he was told. Excitedly brought his head close to her. The sheet under her was already starting to dampen. She must like this as much as Hiccup does. He put his arms around her thighs and got in perfect place. Just as Astrid told him, he got to work.

He started slow, licking lightly along her outer walls, teasing in strokes. He couldn't calm himself and quickly started to get into it more, moving around her vulva, licking, kissing and sucking lightly at her mound. Her breath was starting to heave and she made to grab and pull on his hair but she only rested her hand there, tangled in layers of brown. Petting him lightly. He moved up toward her clitoris after feeling her increased wetness and throbbing walls, he started lavishing the small nub with attention. Hiccup licked in strokes, he changed motions, sped up when her voice wavered, slowed down and changed something when she calmed down, he was so focused on her and bringing her closer and closer to pleasure that he almost didn't feel her tugging sharply at his hair, with the sharp pain on his head he came back to his senses -but still focused on pleasing her- he listened to her breath hitch and he felt her walls close and throb faster around his tongue. Her hips shook, she shuddered, and she pulled harder on his hair, meaning to or not, as she came.

After a few moments she eased up on his hair and her breath stabilized. Hiccup looked up at her glowing red euphoric face, as sweat dripped down, she was signing softly with such ecstasy on her face.

“Wow Hiccup that was one of the best blow jobs you've given yet.” She praised petting his head.

 

“Okay get on the bed,” Dropping right back into her dom voice. She wandered off into the bathroom. “and no touching yourself.”

Astrid seemed to take an agonizingly long time in the bathroom. Hiccup squirmed and squeezed his thighs together, whining and looking down at his trapped boner, the tip still wet in the panties.

_Please hurry up Astrid oh my god._

It certainly seemed to be a long time before she appeared again. Hiccup's mouth wide open at the image before him. Astrid was wearing some sort of harness panties. Harness panties with a yep with a bright purple dildo. That was a strap-on she was wearing. Yep. His fiancee was wearing a strap-on dildo. And she was still so damn hot.

They've talked about trying out Hiccup's ass a few times before, the young man had tried his own fingers before with pleasing himself. He told Astrid it was pretty nice and everything (probably couldn't beat her womanly aperture though). But he wasn’t expecting Astrid to actually surprise him with a strap on that she was planning on spearing him with.

Oddly he did not feel apprehensive like he thought he would when he imagined a real scenario before. Because come on, of course he's thought about it even if he wasn't expecting it. The brunette was actually excited for it, or at least his _little Hiccup_ was.

He was starting to like this surprise.

Astrid cleared the space between them and pushed Hiccup down on the bed. She spoke to him about if he liked what he saw and if he wanted to try it out. He agreed to it but never looking at her face, he was rudely focused on her crotch. A moment ago his face was there and she was shaking, now there is a purple erection that would be inside him soon. _Oh yeah that was going inside me_ , Hiccup thought and chuckled. He didn't even know if he was more excited or it was nerves. Either way he was still hard and he really needed to get it on. The tightness of the panties had kept him throbbing for attention while Astrid was away.

Before Hiccup knew it he was on his back and Astrid had one... no two, yep that was two fingers inside of him, smothered in warming lubricate. God it was nice. He wondered why more guys didn't let their ladies do this for them. Astrid asked how Hiccup felt and if he was ready to try. He was amazed by how fast he said yes to her.

She pulled a condom over the toy covered it in lube, so much so that it was dripping with the slick liquid. After a few breathes -moving the panties to the side for access- Astrid slid the toy in with a kind of popping sound. They both laughed. It was an odd feeling that stung a little at first but it soon eased. He has never really put anything up there before. Just a finger or two.

“Ready?” 

“God yes, please!”

So she did, she started slowly at first, making sure Hiccup was completely comfortable and pleasurable. Yes he was pleasurable, he was moaning and griping the sheets as she bucked the toy into him. She had said she had gotten it at a, well a sex shop, near the mall. The place was called ' _Under the Bed_ ' or something similar. Run by this insanely dominate guy with his pale as hell sub on a leather leash, both where decked out in black leather, and Astrid said she could have sworn the man was wearing yellow coloured contacts. He helped her pick everything out and instructed her on how to use it. He'd have to bake the guy a pie or something.

Hiccup felt his abdomen spark and quickly he snaked his hand under the panties to stoke himself in rapid repeat. Astrid's thrusts where glorious, she was doing such a great job, propped up over him, gripping his thighs as she rutting him, she was getting breathless from the effort. _She wasn't used to having a dick._ He laughed to himself.

Hiccup was getting so close he was about to reach it, he started gasping out his fiancee’s name as he pumped harder. Heat soon shot through him, he shuttered violently, releasing all over his hand and filled his panties.

Astrid pulled the toy out, Hiccup shivered still in an excellent daze, chest heaving and sweat dripping.

He felt amazing, he was coming down from the release but everything was tingling and sparkling so wonderfully. He had the stupidest look on his face as he looked up at Astrid.

“So babe, how was the surprise?”

 


End file.
